2,4-Dichloro-7-methoxyquinazoline Chemical Properties

Melting point:

121-121.5 °C

Boiling point:

316 °C

Density 

1.450

Flash point:

145 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.26±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C9H6Cl2N2O/c1-14-5-2-3-6-7(4-5)12-9(11)13-8(6)10/h2-4H,1H3

InChIKey

DJLGBZOLTZXCHN-UHFFFAOYSA-N

SMILES

N1=C2C(C=CC(OC)=C2)=C(Cl)N=C1Cl

Safety Information

HazardClass 

IRRITANT

2,4-Dichloro-7-methoxyquinazoline Usage And Synthesis

Chemical Properties

White flocculent solids

Uses

2,4-Dichloro-7-methoxyquinazoline is a useful reactant for the preparation of 2, 4-?diaminoquinazoline derivatives which is being study for a potential to be a potent PAK4 inhibitors.

Synthesis

General procedure for the synthesis of 2,4-dichloro-7-methoxyquinazoline from 7-methoxy-2,4(1H,3H)-quinazoline dione: 7-methoxyquinazoline-2,4-diol (3 g, 15.6 mmol) was mixed with phosphorochloridic acid chloride (10 ml), and the reaction was stirred under reflux conditions overnight. After completion of the reaction, the mixture was cooled to room temperature, slowly poured into ice water and the pH was adjusted to 7-8 with sodium bicarbonate solution.Subsequently, the aqueous layer was extracted with dichloromethane, the organic layers were combined and dried with anhydrous magnesium sulfate. After the solvent was removed by concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluent ratio: n-hexane/ethyl acetate=10/1) to afford the target product 2,4-dichloro-7-methoxyquinazoline (0.64 g) as a white solid.1H NMR (400 MHz, CDCl3) δ 8.12 (d, 1H), 7.37-7.20 (m, 2H) 3.99 (s, 3H).

References

[1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 7021 - 7032
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 1, p. 144 - 158
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1452 - 1465
[4] Patent: US2016/90374, 2016, A1. Location in patent: Paragraph 0218; 0219

2,4-Dichloro-7-methoxyquinazoline(62484-31-5)Related Product Information

• 2-Chloroquinoline
• 7-Methoxy-4-quinolinol
• 6-BROMO-4-HYDROXYQUINOLINE
• 6-BROMO-4-CHLOROQUINOLINE
• 4-HYDROXY-6-METHOXYQUINOLINE
• 7-(TRIFLUOROMETHYL)-4-QUINOLINOL
• 4-Chloro-7-methoxyquinoline
• 2,4-Dichloro-6-methoxyquinazoline
• 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
• Quinazoline
• Cefazolin
• Sulfaquinoxaline
• Cefazolin sodium salt
• 2,4-Dichloro-6,7-dimethoxyquinazoline
• 2,4-Dichloroquinazoline
• 6,8-DICHLORO[1,3]DIOXOLO[4,5-G]QUINAZOLINE
• 2,4-Dichloro-7-methoxyquinazoline